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Sears Holdings Blueprint for Tax-Efficient IRA Withdrawals

“Sears Holdings employees who work with a legal or tax advisor to create a structured drawdown strategy—aligning withdrawal sequencing with projected income needs and anticipated tax law changes—can help mitigate their lifetime tax burden.”— Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement.

“By working with a legal or tax advisor to thoughtfully sequence withdrawals from taxable, tax-deferred, and tax-free accounts—and incorporate Roth conversions in low-income years—Sears Holdings employees can help mitigate their retirement tax burden.”— Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

Tax-efficient drawdown strategies for retirement savings
Managing required minimum distributions to help control taxes
Optimal asset location techniques for after-tax returns

Although taxes can erode a sizable portion of retirement assets, Sears Holdings employees can benefit from a systematic strategy known as tax-efficient drawdowns to help preserve more of their savings.

There are distinct tax treatments for different retirement savings vehicles—tax-deferred accounts (such as traditional IRAs and 401ks), tax-free accounts (like Roth IRAs), and taxable brokerage accounts. Taking funds from the wrong bucket at the wrong time may trigger unnecessary taxes, push income into higher brackets, or even increase Medicare Part B and D premiums. Crafting a withdrawal sequence that aligns account types with income needs and anticipated tax liabilities can help to optimize post-career income.

Important Takeaways

- A planned withdrawal order can help extend the longevity of your retirement portfolio.

- Withdrawal timing and tax impact differ across tax-deferred, tax-free, and taxable accounts.

- Capital gains management and required minimum distribution (RMD) planning play a pivotal role in overall tax obligations.

- Personalized strategies—based on income profiles, asset allocations, and health considerations—help align outcomes to individual needs.

What a Withdrawal Sequence Means

A retirement drawdown involves withdrawing money from your investment and retirement accounts—such as taxable brokerage accounts, 401ks, Roth IRAs, and traditional IRAs—to fund living expenses after work ends. Research indicates that a systematic hierarchy of withdrawals from these accounts, based on their tax treatment, can extend retirement savings by three years or more. ¹

Tyson Mavar, a financial advisor with Wealth Enhancement, explains the thinking behind this strategy. When retirees withdraw funds from taxable accounts, taxes apply only to capital gains, which are generally taxed at favorable rates (0%, 15%, or 20%, depending on total income). Withdrawing these funds while still in your earning years could help mitigate your overall tax burden. For their part, funds drawn from tax-deferred accounts (such as 401ks and traditional IRAs), are typically taxed at ordinary income tax rates—so these withdrawals may make more sense during lower earning years. Finally, Roth IRAs allow for tax-free withdrawals. Delaying withdrawals from these tax-favored accounts gives them more time to grow tax-free.

To determine the best withdrawal sequencing for your needs, it's important for Sears Holdings employees to consider their individual circumstances. For example, partial Roth IRA distributions after the five-year holding period may be advantageous in early retirement years if your taxable income is particularly low and could help to manage future RMD requirements.

Managing the Necessary Minimum Distributions

Current IRS rules require account owners to begin RMDs from employer-sponsored plans and traditional IRAs by April 1 of the year after they turn 73 if they were born between 1951 and 1959. For those born in 1960 or later, RMDs start at 75. If not managed carefully, these mandatory distributions—treated as ordinary income—can raise annual tax bills for Sears Holdings employees.

In the decade leading up to RMD age, Mavar often advises clients to consider Roth conversions. Because Roth IRAs do not mandate RMDs, shifting assets from a traditional IRA to a Roth IRA allows your money to grow tax-free. That said, the conversion itself incurs income tax at current rates. Strategic timing of conversions in low-income years may help control taxable income and may lower total lifetime taxes.

Optimizing Asset Placement

Asset positioning—placing investments in the most tax-advantageous accounts—is key to efficient drawdowns. Interest-generating investments (like bonds, actively managed mutual funds, and real estate investment trusts) often produce income taxed at ordinary rates, making them ideal candidates for Roth or tax-deferred accounts. Conversely, tax-efficient holdings (such as municipal bond funds and broad market index funds) can be held in taxable accounts, where favorable dividend and long-term capital gains rates apply.

Customization and Comprehensive Planning

No single drawdown plan fits every retiree. A thorough strategy considers factors like current and future income needs, Social Security claiming tactics, medical expenses, legacy goals, and potential tax law changes. Incorporating these elements into a cohesive plan can position Sears Holdings employees to preserve assets for lifelong income and intergenerational wealth transfer.

At Wealth Enhancement, Tyson Mavar and his team specialize in designing customized withdrawal plans. Leveraging their deep knowledge of tax law, investment management, and retirement income planning, they guide clients through complex choices—such as adjusting withdrawals to mitigate Medicare surcharges and evaluating Roth conversions against market conditions.

In Conclusion

After a career of diligent saving, you deserve a retirement plan that helps you keep more after-tax income. When thoughtfully designed and personalized, tax-efficient drawdowns can help make funds last longer. Working with an experienced advisor to navigate capital gains tax management, RMD rules, account hierarchies, and evolving tax laws can yield real savings and greater financial flexibility.

Learn how to navigate RMD implications, manage taxable income, and preserve lifetime savings through strategies like qualified charitable distributions, Roth conversions, and optimized drawdown sequencing. It’s akin to conducting a symphony: you start with the soft strings of taxable brokerage gains, introduce the warmer woodwinds of tax-deferred accounts, let your Roth “brass” soar tax-free, and weave in timely “Roth conversion” solos before the RMD percussion begins—making sure every instrument complements the ensemble without overpowering it.

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Sources:

1. Financial Analysts Journal. ' Tax-Efficient Withdrawal Strategies ,' by Kirsten A. Cook, William Meyer & William Reichenstein. 28 Dec. 2018.

Other Resources:

1. Sumutka, Alan R., Andrew M. Sumutka, and Lewis W. Coopersmith. “Tax-Efficient Retirement Withdrawal Planning Using a Comprehensive Tax Model.” Journal of Financial Planning , vol. 25, no. 4, Apr. 2012, pp. 41–52.

2. Neufeld, Dorothy. “How Required Minimum Distributions Impact Your Traditional IRA Balance.” Investopedia , 14 Apr. 2025, https://www.investopedia.com/required-minimum-distributions-impact-traditional-ira-balance-11711080 .

3. Vanguard Group. “Asset Location Can Lead to Lower Taxes.” Vanguard , Aug. 2024, https://investor.vanguard.com/investment-stewardship/asset-location .

4. Morningstar Editors. “How to Spend From Your Portfolio Tax-Efficiently in Retirement.” Morningstar , Nov. 2024, https://www.morningstar.com/articles/2024/11/how-to-spend-tax-efficiently .

5. Kitces, Michael. “Navigating Income Harvesting Strategies: Harvesting (0 %) Capital Gains Vs. Partial Roth Conversions.” Kitces.com , 22 July 2020, https://www.kitces.com/blog/navigating-income-harvesting-strategies-harvesting-vs-roth-conversions .

How does the Sears Holdings Pension Plan differentiate between normal retirement, early retirement, and late retirement options for Kmart participants? In what ways do these options influence the retirement planning process for employees of Sears Holdings, and what specific considerations should Kmart employees be aware of when choosing one of these retirement paths, particularly in relation to their vested status?

Differentiation of Retirement Options: The Sears Holdings Pension Plan offers distinct options for normal, early, and late retirement. Normal retirement is available at age 65 or after five years of plan participation, whichever is later. Early retirement can be taken from age 55 but before 65, provided the employee is vested, with benefits subject to actuarial reduction unless certain conditions are met (like having at least 90 points, which is a sum of age and years of credited service). Late retirement pertains to any retirement after the normal retirement age, with pensions recalculated to reflect the delay in benefit commencement.

Considering the frozen status of the Sears Holdings Pension Plan, how does this impact the benefits eligibility for Kmart employees, and what implications does it have for their retirement savings strategies? In what ways should current employees factor in this frozen status when evaluating their overall retirement readiness and potential alternatives outside of the company plan?

Impact of Frozen Status: The freezing of the Sears Holdings Pension Plan on January 31, 1996, means that there have been no new accruals of benefits or participants since that date. For Kmart employees, this impacts their benefits eligibility by capping the pension benefits at levels earned up to the freeze date. Employees need to consider this stagnation in benefits when planning for retirement, potentially seeking additional retirement savings avenues to bridge any shortfall.

What are the essential calculations involved in determining the retirement benefits under the Sears Holdings Pension Plan for Kmart employees? Specifically, how do the Career Average Pay and Final Average Pay formulas come into play, and what factors should employees consider when estimating their future retirement payouts?

Essential Calculations for Retirement Benefits: Pension benefits for Kmart employees under the Sears Holdings Pension Plan are calculated using either the Career Average Pay or the Final Average Pay formulas. These calculations take into account an employee's years of credited service and compensation up to the freeze date. Factors like estimated Social Security benefits and specific formulas (such as a deduction based on Social Security benefits under the Final Average Pay formula) play crucial roles in determining the final pension payout.

How can Sears Holdings employees best navigate the process of applying for benefits under the Pension Plan? What specific steps should participants take to ensure their applications are processed correctly, and what important deadlines should they be aware of to avoid any negative consequences on their retirement benefits?

Navigating the Benefits Application Process: To apply for pension benefits, employees must submit a formal application, ideally 30 to 90 days before the intended commencement date. It is crucial to ensure all personal information, including marital status and spouse details, is up-to-date to avoid delays or inaccuracies in benefit processing. Missing application deadlines can lead to postponed benefit payments or unwanted default options.

In what situations can Kmart employees expect to receive a Deferred Vested Pension, and how is the calculation for this pension affected by their previous employment and vesting service? Employees should be aware of the important factors influencing their eligibility and the steps necessary to maintain their retirement benefits after leaving the company.

Eligibility and Calculation for Deferred Vested Pension: A Deferred Vested Pension is available to employees who leave the company after becoming vested but prior to qualifying for retirement. The calculation mirrors that of a normal retirement pension, with possible early commencement reductions. Understanding the timing of benefit commencement and the potential reductions for early start is vital for planning.

How does the Sears Holdings Pension Plan address tax considerations for employees receiving both monthly payments and lump sum payments upon retirement? What tax implications should Kmart participants be aware of, particularly in relation to IRS rules for distributions and potential penalties for early withdrawal?

Tax Implications of Pension Receipt: Pension payments, whether monthly or lump sum, are subject to federal taxes. Monthly benefits are taxed as ordinary income, while lump sums might be eligible for special tax treatments or rollover options to defer taxes. It’s important for Kmart employees to consider these implications and possibly consult with a tax advisor to optimize tax liability.

What are the rights and protections afforded to Kmart participants under the Employee Retirement Income Security Act (ERISA) as they navigate their retirement benefits with the Sears Holdings Pension Plan? How can employees leverage these rights to ensure they are receiving all the benefits to which they are entitled?

ERISA Rights and Protections: Under ERISA, Kmart employees are entitled to certain rights including the ability to appeal denied benefits, access to plan information, and assurances of fair and equitable treatment of their benefits. Leveraging these protections ensures that employees receive all due benefits.

What steps should Kmart employees take to update their personal information to ensure they continue receiving their benefits without interruption, especially in the context of missing participants or uncashed checks? What resources and contacts at Sears Holdings are available to assist with these updates?

Updating Personal Information: Maintaining accurate personal information with the pension plan is crucial for uninterrupted benefit payments. Employees should promptly update changes such as address, marital status, or beneficiaries to prevent issues with benefit distributions or lost checks.

How does the process of transferring between affiliated employers impact pension benefits for Kmart employees under the Sears Holdings Pension Plan? What considerations should be taken into account concerning Credited Service and Vesting Service during such transfers, and how can employees ensure they do not lose any entitled benefits?

Impact of Transfers Between Affiliated Employers: Transferring between Sears Holdings’ affiliated employers can affect pension benefits differently depending on whether the employer participates in the pension plan. It's essential to understand how such transfers impact credited and vesting service accruals.

For Kmart employees seeking more information about their benefits under the Sears Holdings Pension Plan, what is the best way to contact company representatives? How can they effectively communicate their questions or concerns to ensure they receive accurate and timely information regarding their retirement benefits?

Contacting Plan Representatives: Kmart employees seeking clarity on their pension benefits should contact the Sears Holdings Pension Service Center. Effective communication, including prepared questions and necessary documentation, will aid in obtaining accurate and comprehensive information.

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For more information you can reach the plan administrator for Sears Holdings at 3333 beverly road Hoffman Estates, IL 60179; or by calling them at 1-800-697-3277.